Shopping for women’s clothes is already a complete pain in the ass but through patience and knowing where to look you can find great things for a good amount of money.

Something to keep in mind if you aren’t done transing is your size might (probably will) change throughout your journey. HRT does a decent amount so until you’re at a stable body type/size you’re happy with I would avoid spending too much money on items that could end up not fitting properly in the future. 

Shopping in the men’s section of stores sucks because everything looks the same. Same colors, same cuts, same boring. However one of the benefits of shopping in the men’s section is that sizing is also the same across brands! This is not even remotely true at all for women’s clothes since sizing isn’t even always the same within a singular brand.

Always always always check the size guide for every individual item you can because it really could be different every time. 

That’s why shopping in person is something I highly recommend. It’s going to be very anxiety inducing at first but eventually you’ll learn not to care. If you’re worried someone might recognize you then you can always drive somewhere far enough away that it won’t happen. 

The main benefit of trying clothes on in person is that you can instantly see how it fits YOUR body. A lot of clothes online don’t even get modeled these days so it’s super hard to gauge how well it will fit on you. There have been times where I wanted to buy something but went to try it on in person and left it behind because it looked awkward on me compared to the models online.

You’ll almost certainly hear the people at the store tell you eventually “The men’s section is over there.” and I’ve always found the best response to things like that is “I know” or “Yeah, but it’s just really boring”. People do shop for their SO sometimes or simply don’t like what’s offered in the men’s section so these responses can dismiss people looking over your shoulder. I wouldn’t say you’re looking for a gift though; unless you want them to help because it implies you’re shopping in a section you’re never normally in. 

This tip is especially true for shoes and rings because those are a completely different beast when it comes to sizing. For my fingers on my left hand I’m a size 8, 8.5 or 9 all in one brand, with 8.5, 9.5 and 10 on my right hand. Shoes differ a lot in shape and quality and because most women’s shoes are ridiculously tiny, it will be far more important to find something that fits than something that destroys your feet but looks pretty. Style codes (the measurements for this piece) can be found on a brand’s website and frequently in a URL or the tag itself. If the measurements of an item seem unreliable, finding size charts online for the style code can be a life saver. 

One dress might look great on someone who is 5’3 and petite but not someone like me who is 6’3 and large-ish. Seeing the item in person also gives you the chance to feel the fabric and see if it’ll be comfortable for you, see the actual colors of the garment, and if it’s good quality. Too many times will an item be super thin and sheer ordering it from online which doesn’t typically happen with men’s clothing. You will come to learn what high quality clothes feel like overtime but because you get to feel them in your hand you have more assurance. Plus going to higher end brands just to browse for an idea and feel won’t harm anyone (but be prepared for annoying sales people).

The added benefit of not having to deal with final sale items/returns is also super nice (yay mindful sustainability)! 

Another important aspect is finding brands that fit you. Buying new things from different places all the time is time consuming and expensive but buying second hand can be tricky, (eventually I’ll have a guide for that), so finding brands that work for your style and body can be a lifesaver. Brand loyalty is fine so long as the quality and service merits it. Generally speaking it also makes it much easier to pair things together if they’re all from the same place. Most brands will stick with one aesthetic so all their pieces mesh well together, making your life easier if you stick with them.

Most of my shoes are converse because I know they fit me and go with most of what I wear.

For example I have a lot of clothes from places I used to work at because they fit my style, are flattering for my body and are good quality. An added benefit is knowing my size for those brands being I can buy items second hand and not worry about how they might fit me which can lead to some amazing deals on clearance. 

All of these items are from the same brands for each photo. They all have the same vibe to one another and so pairing is easy.

Clearance deals are MUCH easier to find when seasons start changing, and the best deals are usually 4-6 months after the season happens. Looking up past sales using forums or website archivers can also be a good way of knowing their highest markdowns. Generally the best deals for Fall stuff will be in April, Winter stuff in June, Spring stuff in late September, Summer stuff in November. Just keep in mind that sizing will be harder to find as supply depletes.

Sometimes leaving an item in the cart for long enough will get you a free coupon!

Newsletters are also a good way of being sent deals that go unadvertised elsewhere. Setting up a specific email account or filter for those with keywords like “60%” can be an easy way of avoiding the digging.

Thrifting is another great way of shopping because you get exposed to many different brands and styles. Prior to the pandemic, things were much better as thrift stores now are flooded with fast fashion garbage and it’s a trendy activity for people to find nice things and resell them instead of wearing them. I however still think it can be a good way of finding pieces you otherwise may never have seen. It’s important to go into thrifting with only a general idea of what you want in mind because if you look for a specific print or fit then you will almost always walk out empty handed. When I thrift I usually just go there in mind with ideas like ‘a nice blouse’ or ‘boots that aren’t the color black’ because keeping an open mind is what lets you find treasures. 

Because the nature of thrifting is sparse in true options, sizing can be difficult. However the low cost of thrifting pieces also means you can spend that money you saved  on getting that item tailored! This GREATLY improves the look of some things from fitting ‘meh’ to ‘slay queen’. An important note is that there is more a seamstress can do than just tailoring it, adding darts is far more important in my opinion if you want something to truly fit well, like on this white shirt.

If you find an item you really like you can get the same thing in different colors too without the worry of fit. A lot of colors are viewed as seasonal, like brown in the fall, so it’s important to check in on things every few months. Seasonal colors also go on sale when the season for that color ends while all year round colors like black, white, and navy might never go on sale if you were hoping they might, so if a brand has a special sale where everything is 20% off for example, those non seasonal colors might be the lowest price you can get them.

Speaking of colors, having what’s called a ‘capsule wardrobe’ is super useful for picturing how items might fit into your style. What this means is having a strong base of essential items that you can all mix and match, and generally, not a lot of clothes. For example black and white button up shirts along with black and white pants can literally be all you need to work in an office setting. Having black and white means either your top or pants can be any color and they will almost always match. 

Here is an example with these tops I have with a single pair of jeans.

Lastly, compare prices across different websites. This may sound simple but because of how brands operate it benefits them to be sold in more than one location. Their own brand website (if they have one) will most likely be the cheapest since they don’t have another retailer reselling their merchandise and can keep a higher percentage of the profit margins. This even applies to consignment because some individual sellers might be delusional and others have no idea how good of a deal they’re offering. This coat for example was listed on the same website, but with different listings; the pictures didn’t match up because of how it was photographed (on the left) but I was willing to investigate. It retailed for about 1500$, I got it for 200$ instead of 400$ because I was willing to match up the details through the buttons and sleeve elements, confirming it was the same item.

• Shop in person! This may be harder for some people but it makes things much easier when you can try things on. Even if you don’t intend on buying things in person, trying clothes to see how they fit makes the world’s difference when you buy things online so you don’t have to return stuff constantly since you’ll know what size you are.
• Stick with brands you like and that fit you. Buying things from random brands everytime is a sureway to be disappointed, especially if you shop online. Finding places/brands that work for you is hard, but well worth the time and money once you find them.
• Familiarize yourself with national upper scale brands. Finding these deals with items that are used and online will be easier than on sites like facebook marketplace. Because they don’t have international recognition like they do locally, they will often be consigned for cheaper online than locally.
• Avoid cheap feeling clothes. If it doesn’t feel good to wear, you won’t wear it. It’s much better to save your money for nicer things you love and wear often. At the start don’t be afraid to experiment with cheaper items but once you’ve found your aesthetic, try to be more thoughtful about what you spend your money on.
• Thrift! Don’t go thrifting with anything other than a category in mind (such as jeans). You won’t find your dream green floral asymmetrical midi skirt the first time you go if it all, so keep your hopes and dreams broad when thrifting. Simple ideas like: ‘I want a nice blouse’, is good enough. I’ll have a more in depth post about thrifting eventually 🙂 
• Shop for things out of season. It’s much easier to find sales towards the end of seasons, typical big sales start in June/July for Spring and Summer clothes or December/January for fall/winter. People also typically sell things when they don’t need them, so if you need a winter coat, buy it in the summer.
• Compare across websites. Sometimes brands sell to larger retailers like Macy’s which add an additional markup, going to the brand’s individual site will often be cheaper.