Fall is arguably the best season for clothing. You can go crazy with layering and wear almost everything in your closet. Get out the leather boots, suede Oxfords, woven belts and thick cotton socks. Wear jackets without overheating, or ditch the jacket altogether and throw on a sweater over your dress shirt and tie.
As a modest man, I love autumn. Cool weather means layers, and layers mean you can wear all those button up shirts that don't really fit (throw on a cardigan = problem solved). Also, boots are some of the most comfortable and stylish shoes you can find, and they have nice thick soles.
(Note: I would never buy a pair of shoes just because they had thick soles, but I won't complain about that extra half inch a good pair of boots provides.)
Here are some things to keep in mind when putting together your fall getups:
While summer is all about cotton and linen, autumn calls for suede, flannel, wool, corduroy and tweed. Mix and match these materials, and keep the thinner materials closer to your body (for example: cotton henley, flannel button up, leather jacket).
Emulate nature with deep reds, greens, browns, tans, oranges and creams. Swap out your standard brown leather belt for a colorful woven variety, like these (roughly $10 from JCP).
It's okay if your closet is lacking in color variety. Don't feel the need to box up all of your blue/grey/black clothes in favor for bright orange everything. You can totally layer up with light grey, navy, charcoal and khaki.
Jackets & Coats
Keep your outerwear fitted and relatively short. Pea coats, for example, shouldn't go past your mid-thigh. Definitely not past the knee. If you can pull off a long coat, more power to ya, but it's not the easiest look for a shorter guy to pull off.
Avoid bulky jackets. For example, padded or “puffer” jackets are very popular right now (they seem relatively timeless, or at least they keep coming back into style). Unlike the ones we saw in seasons past, today's padded jackets are tamer and less, well, padded. Which is great for us svelte gents.
Go with something that doesn't add too much bulk to your frame, like this J. Crew Factory Puffer Jacket (available in XS online and almost always on sale), especially if you have some natural bulk. Stick with simple, understated patterns or solids so don't look like a jerk (the Nike gloves and crotch grab aren't helping, Drake).
If padded jackets aren't your thing, technical or wool jackets are great alternatives. Many come with cool detailing that produces a slightly edgy look. Just don't go overboard and buy someting that's covered in buttons, buckles, flaps and hidden pockets. Zara is making some cool jackets that fit smaller men really well.
Cardigans and merino sweaters are perfect, thin layering essentials. Stay away from cashmere. It's not worth the price tag, and most stores have much less expensive options in cotton and wool. My favorite stores to buy sweaters are (in order from least expensive to most expensive): H&M, J. Crew Factory (XS online only), Express and Peter Manning.
You can go with v-neck or crew neck sweaters. I recommend v-necks to wear over button up shirts. Just make sure the “v” isn't too deep. It will look disproportionate on shorter guys, especially when worn without a button up shirt underneath.
You can also pick up at least one or two pullovers. They make good sweater alternatives, and you can take them off if you get too warm. J. Crew Factory sells XS pullovers that fit my slim 5'6″ frame perfectly.
Boots are the perfect shoes for shorter guys. Every man should own one pair of desert boots. If you don't have any, the go-to DBs are Clarks Desert Boots. J. Crew McAllisters are a lower-profile alternative (available in unisex sizing down to size 4 online), and Cole Haan makes a slightly more formal pair that will last a long time. You can choose suede or leather in virtually any color, but tan or dark brown are safe bets.
Finally, you might need a pair of rain boots, or at least something waterproof. Zappos, Amazon and LL Bean are all good places to look. Don't bother buying expensive rain boots unless you plan on wearing them all day (or live in Seattle…). Just get get a cheap pair and change when you get to work/school.
Hats & Gloves
Depending on where you live, you may not need extra hats or gloves for the transition from summer to winter. But it's nice to have some thinner, lighter alternatives to your big old winter mitts. Gloves are like socks, in that most stores (with the exception of some, like H&M) seem to think every guy has the same size hands. Isn't that ridiculous?
To find something that actually fits your fingers, try unisex or women's gloves. This takes a bit of pride-swallowing, but isn't that what online shopping is for? You can also check the young men's departments.
Any seasonal transition is a great time to modify or even overhaul your wardrobe. If you've been thinking about making some changes or upgrades, do it now! It's also a great time to experiment with new types of clothing and different colors.
Think you're not a cardigan kind of guy? Try one on. Always wear blue? Go find some red/orange/brown/yellow shirts. It's fall, so you'll fit right in. And if you don't own any boots, now is the time to go buy some.
They really are a quintessential part of a man's wardrobe, and you can actually wear them in any season. But they look damn good in fall and winter.
Got questions or suggestions? Leave a comment below, or get in touch!