My Email Playbook For Fashion Brands


Find Free Money In Your Email File With This Email Playbook

In this guide I’m going to cover the pillars of an effective email marketing program for fashion brands. If your email revenue is lagging or you don't know where to start, check your current email strategy against this playbook.

Before we get into it, I want to give a big thank you to our launch partner: TESMO. TESMO is a full-service Amazon management agency for DTC brands.

TESMO specializes in scaling the Amazon channel for tricky categories like fashion. If you've considered launching on Amazon, or are unhappy with the state of your Amazon business, you should reach out to them.

Quick Note: this is the second-to-last week of your free trial of DTC (fashion) Decoded. In two weeks, every other issue of this newsletter will go behind a paywall.

Click here to become a monthly member, or click here to save 15% on an annual membership.

If you implement the tips I share below, you can make back the cost of an annual membership ($50) in less than a week.

First: DON’T Make These Mistakes

Fashion brands typically take one of two approaches when it comes to email:

  1. The brand sees email as an intrusion, mails the list 1x/week or less and email content must adhere to tight creative guidelines that take precedence over usability.
  2. The brand sees email as a “money tree”, mails the list at least 1x/day, schedules extra emails when falling behind daily sales plan and content is repetitive and low effort.


Both of these approaches are wrong. Your email file is a microcosm of your customer file. As I shared last week [link], that means you need to acquire new customers/subscribers to grow. No matter which approach you take, you’ll eventually burn out the list if you aren’t consistently bringing in high quality subscribers.


There is a maximum dollar value the folks on your list will be able to spend with you (few would go hungry to buy a new bag). Your job is to capture as much of that potential value as you can. The “email as intrusion” approach is leaving money on the table, while the “money tree” approach burns out your list prematurely.

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One of the biggest myths in retail: "I can't sell fashion on Amazon."

More than a third of all US apparel sales take place on Amazon, and slightly more than half of US households are Amazon Prime members. Fashion is being sold on Amazon. If your brand doesn't have a presence there you could be missing out on a huge source of revenue.

That said, selling on Amazon isn't exactly easy. Amazon has its own conventions, unspoken rules and best practices. Many brands who think "Amazon can't work for me" are simply ignoring these rules.

TESMO has been helping premium apparel brands scale on Amazon since 2008. They are a full service agency who does one thing extremely well: growing the Amazon channel. TESMO will integrate closely with your team and their senior leaders will be "hands on keyboard" in your account.

Click here to book a call with the TESMO team to discuss the size of your brand's Amazon opportunity.

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What Email Service Provider (ESP) Should I Use?

You should choose an ESP with features that allow you to do everything in this post “out of the box” (i.e. with minimal coding or integration work). This means you want an ESP that integrates directly with your eCommerce platform.

If you’re using Shopify there are dozens of options. If you’re using a different eCom platform, your options are going to be more limited, or potentially non-existent. I’m not going to bash or promote specific software providers here.

The big cost driver for ESPs is contact storage. Most ESPs charge for each subscriber on your list and/or for each email you send. You still get charged for subscribers who have unsubscribed, but whose data remains on your account.

If you want to use your ESP as an archive of everyone who has ever been on your list, it gets expensive. Even if you don’t want to do this, you’ll have to manually remove opted-out users from most platforms.

Run cost projections for any ESPs you’re considering–not just for today’s list size, but for expected list size in 1-2 years. Changing ESPs is painful, and becomes more painful as your list grows, so choose wisely.

Finally: avoid platforms with annual contracts. An annual contract is a good sign that the relationship will be more costly than you anticipate.

How Do I Keep My Emails Out Of The Spam Folder?

If you own a business email address, you know how the channel can be abused by scammers and overzealous salespeople. Major email services like Gmail and Yahoo do their best to keep garbage out of your inbox. If your brand engages in suspicious behavior, you may wind up in your subscriber’s spam folder.

The technical details of deliverability are outside the scope of this post (and frankly, pretty boring), but there are some things you should know:

  • Don’t add people to your email list without at least a single opt-in. I.e. don’t scrape the web for emails, buy lists, or use tech that emails site visitors without an opt-in.
  • Stop emailing people when they’ve unsubscribed, and make it easy to do so.
  • Make sure you have a custom sending domain set up.
  • Don’t try to trick people into opting in or staying opted in.


If you plan to work with an email agency or freelancer, grill them on deliverability and make sure they aren’t using black hat or gray hat tactics to grow the channel.

How Do I Build Emails People Will Actually Read/Click?

Many fashion brands favor email designs that look like magazine ads or editorials: a large image layout where all text in the email is part of the image. This type of email can work well, but I recommend that brands build out at least three templates:

  1. A template that lets you execute the image slice designs described above without hand-coding HTML.
  2. A template where the images, text & CTA buttons live as separate HTML elements, like this.
  3. A plain-text email that looks like it was sent from a friend or coworker (no images, no header or footer).


As your brand does more work with segmentation and personalization, limiting yourself to approach #1 will slow you down.

Most emails are read on people’s phones. You should ensure your template displays as expected on mobile devices and keep these usability principles in mind:

  1. Make sure text is legible on mobile–text in images that looks fine on desktop can be too small to read on mobile.
  2. Make sure that your CTA buttons are large enough to click and read on mobile.
  3. Try to place your first CTA button “above the fold” on mobile, aka put it close enough to the top of the design that no scrolling is required to see it.
  4. Add alt text to your images in case images don’t load due to spotty wifi.
  5. Don’t use image maps; they won’t scale down properly on mobile.

Do I Need To Offer A Discount In My Email Popup?

If you visit any eCom site today, you’ll probably be greeted with a popup asking you to subscribe to the brand’s emails in exchange for some kind of discount on your first order. Most fashion brands want to know if the discount is really necessary.


The answer? It depends. The discount will help you get more prospects opted in to your newsletter. This will give you a short window of incremental opportunity to convert your site visitors with your Welcome series (the window is about a week long).


But you don’t necessarily need a promotion to drive email opt-in; some of your customers will opt into your brand’s emails at checkout. If you decide to forgo the discount, you’ll have to work from the assumption that most of your new subscribers will come from customers checking out.


Remember: people opt into your email list because they think they’re getting something of value in return. When a brand runs a standard email strategy, that “something” is typically the promise of discounts, now or in the future.


Your brand’s biggest fans and advocates will stay on your list just to read whatever content you put out, but that represents a small portion of your audience. The more you’re able to entertain or inform with your email content, the less you’ll need to rely on discounts to keep folks opted in.

TL;DR: it’s probably not worth it to run an email opt-in popup if you aren’t offering a discount. But test it for yourself. I’ll show you how, step-by-step, in a future issue.

How Many Emails Should I Send?

You should email the engaged segment of your list at least two to three times per week. You can mail your most engaged subscribers every day if you have the content to support that.


The best way to approach email cadence is to break out your list based on subscriber engagement like this:

  • Most engaged: email every day (or more)
  • Average engagement: email 3-4x/week
  • Low engagement: email 1-2x/week
  • Stopped engaging: email 1x/month


Within each segment, prioritize the most commercial messages. The day of the week you mail each segment doesn’t matter.

For example: if you’re launching a 4-day promotion next week, include all four segments in the launch email. Include Most, Average and Low in the “last day” email. And include Most & Average on every day the promo runs.


How you define these segments is up to you. I typically measure engagement based on days since the last email click and/or open + time since opt-in.

The “Most Engaged” segment needs to make a certain number of clicks within the past week (implies they’re opening/clicking several emails per week).

What Kind Of Content Should I Send?

Let these principles guide your email content calendar:

  1. If you’re in a full price period, emails featuring best sellers will always perform best.
  2. Email is a great low-cost channel for introducing new products and testing new merchandising stories/angles.
  3. People tend to buy more of what they already bought until they become “loyal”.


You’ll do well with a mix of the following message types:


Launch Announcements: When you’re launching a promotion, dropping a new collection or a product is coming back into stock, let people know.


Best Sellers: Highlight individual styles or sitewide best-sellers. Always great for conversion rate and revenue.


Social Proof: Showcase your most popular products and illustrate why people love them by featuring customer reviews, UGC, influencer photos, etc.


Category Guides: Feature the best selling products in each of your major categories. Try to feature at least 9-12 products in the email.


Product Deep Dives: If you have a special manufacturing process or product details that set you apart from the competition, highlight them here. Works great when paired with a best seller.


Impulse Buys: Feature 3-5 items under $50 (or at the low end of your AUR range) and try to put a story around them. This can drive some incremental low-friction conversions. Consider pairing with a free shipping offer if unit economics allow.


Use Case Stories: Give subscribers options for common scenarios–wedding guest, wear to work, packable vacation wardrobe, etc. Make relevant to your customer’s interests and your assortment.


Trend Stories: These don’t work well unless you’re featuring a real trend–you can’t just pick a theme from your collection and call it a trend.

Personalized Recs: A grid of 12-16 products. Ideally these are algorithmically generated based on the subscriber’s site browse data. But you can just do a grid of best sellers and call them recs.

Landing Page: Use a traditional paid social landing page layout to sell an individual product or category. Include concepts like features & benefits, reviews, social proof, “how it works”, etc. Click here for an example.

You can combine multiple concepts to build out your content calendar. Ex. Best Sellers x Social Proof or Trend Story x Product Deep Dive.

Should I Send “Content” Emails?

Many brands I’ve worked with try to integrate “pure content” into the email calendar. These are emails that attempt to educate or entertain with no sales objective. This is a valid strategy, but brands should keep a few things in mind before they try it:

First: No one wants to read a content email where the text is part of an image, in low contrast, with a tricky “brand” font. If you want people to read these emails, use a template where the text is rendered in HTML.


Second: These emails won’t perform as well as product-focused emails when measured on a last-click basis. That doesn’t mean they aren’t worthwhile. Pick a reasonable objective for these emails before you start, along with a way to measure it.


Third: Don’t phone it in with the writing. More people will read these emails if the topic is relevant and the content really is entertaining. Look to Substack fashion newsletters and brands like Tory Burch for inspiration.


Sidebar: emails about your brand history, collection inspiration or the latest campaign will only appeal to your super fans, who are a small segment of your audience.


In my experience, this type of content is not worth sending. If you feel strongly about it, send it to your VIPs via a plain-text email directly from the founder. Or publish it as a blog post on your site and link to it at the bottom of a product-focused email.

Remember, your subscribers’ hands are forever hovering over the “unsubscribe” button (or worse, the “report spam” button). And they’re always wondering “what’s in it for me”?

How Should I Segment My List?

Segmentation is a tradeoff between effort (building multiple versions of an email creative) and payoff (incremental revenue).


Segmentation is only worthwhile if you’re able to send each segment different email content and that difference is meaningful enough to drive incremental sales. I’ve seen too many brands build and manage 5+ segments, only to send everyone the same content at the same frequency.


Here are a few segmentation frameworks that I’ve found to be worthwhile:


Email Engagement: as explained in the prior section


Prospect v Nurture v Loyalty: Breaking your reporting into segments based on lifetime orders placed (0 vs 1-2 vs 3+) can help you understand what content resonates with customers at different stages of the life cycle.


VIP Outreach: Segment out the top 10% of your customers based on last 12 month spend net of returns. Give this audience early access to sales, special promotions, notes from the founder, etc. Ask them for feedback directly.


Key Concern/Interest: If there are distinct use cases in your product assortment, or shoppers come to you for several distinct reasons, speak to those reasons. A dress retailer might have a client base that spans young single women looking for “going out” dresses and older women shopping for family events.


Try to collect this information at opt-in via popups or surveys. Some brands might not have distinctions like this, or might be uncomfortable with making them explicit.


Mens v Womens: This is only worth it if there is a roughly 50/50 split between mens and womens buyers in your email file. Try to get shoppers to express their preference at opt-in and then honor that preference.


Unless you have a list of 100k+ active email subscribers it isn’t worthwhile to segment based on prior purchase history. If you keep your email content relevant, it doesn’t matter. Excluding (for example) polo shirt buyers from an email about khakis is a missed opportunity to cross-sell.

What Email Automations Do I Need?

There are 5 core email automations every brand should have in place, regardless of the size of your email list:

Abandoned Cart: triggered when a site visitor adds product to cart but doesn’t convert. Can include an offer, but that isn’t necessary. In absence of an offer, meet objections or feature alternative products they might like.

Welcome Series: triggered when a site visitor who has not converted opts into your list, usually via a popup. You have 48-72 hours to convert these folks before they start to tune you out, so make sure to send at least 3-5 emails during that time, especially if your popup features an offer.

Post-Purchase Series: triggered after a site visitor makes their first purchase. These emails should reassure them that they made the right decision, provide any critical onboarding info (ex. how to use the product), and show them other products they might like to buy.


At Risk Of Lapsing: triggered when a customer goes a certain number of days without purchasing. The precise timing can be algo-driven [link] or based on average customer behavior. The email should break through the noise, ask if any issues are preventing a second purchase, and potentially offer a discount.


Back In Stock: if it’s technically feasible with your ESP and eCom platform, you should surface an email opt-in when individual SKUs are out of stock and trigger an email when the SKU in question comes back into stock.


There are a few common mistakes I see fashion brands make when it comes to automations:


Not Sending Enough Emails: Your Welcome series should contain at least 5-10 emails. The first 2-3 emails should go out within 48 hours of opt-in. The entire series should play out over the course of 7-10 days.


Your Post-Purchase series should contain 8-10 emails or more. The first email should go out immediately post-purchase. The entire series should play out over the course of 2-3 weeks.


All the other series should contain at least 2-3 emails.


Content/Audience Mismatch: Prospects don’t want to learn more about your brand yet, unless that knowledge answers the question “what’s in it for me”? The Welcome Series should answer questions like Why should I buy [best seller]? Will [category]’s quality hold up? What other products does this brand sell?


Your VIPs care about deep brand narratives–your founding story, your latest campaign or runway show, etc.


Loyal customers–those with 3-4 lifetime orders or more, are much more likely to join your loyalty program, participate in a referral offer, or join a brand’s secret Facebook group. Keep these messages out of your Welcome & Post-Purchase Series.

Don’t Waste Your Time With…

A/B Testing things that don’t matter. “On model vs flat” doesn’t matter. “Campaign image A vs campaign image B” doesn’t matter. Most subject line testing doesn’t matter.


Most effective email A/B tests are pattern disrupters e.x. a 2-word subject line when you usually send 14 words, or a plain text email when you usually send image slices. But when these disruptions become standard practice, they lose their effectiveness.


Email automations if your brand is doing full-file sends 1x/day or more. Automations won’t break through the noise with enough clarity to drive any lift in sales. Exception = when you exclude folks in flows from your daily sends (but test it for yourself).


Offer testing if your offers aren’t as deep or broad as whatever sitewide offer happens to be running.


Send time testing. Your subscribers will open your emails at whatever time you send them regularly. There isn’t a magical “optimal send time” that will help you “beat out the competition”–everyone’s inbox is different.


The best way to get “on top of the inbox” is to send email content that people seek out proactively. The second best way is to send multiple emails a day, to increase the odds that you’re at the top whenever someone happens to check their email.


Testing email optimization tactics if your new customer count is flat or declining. In this case, your email revenue is down because customer acquisition is down. Tactics are a bandaid on a bullet wound.


Hand-coding emails in HTML. Build out drag and drop templates for everything. Your ESP should make it simple to build these templates and provide a streamlined WYSIWYG editor.


Sweepstakes as a list building tactic. Your subscriber quality will be low. This goes for cross-brand giveaway promotions too.

Software service contracts with a duration of six months or more.


Email agencies who charge a percent of “revenue generated”, and then use your ESP’s in-platform analytics to measure that revenue.

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